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Article Dans Une Revue CrystEngComm Année : 2024

Shortening C≡N···Br-C sp3 halogen bonds via π-stacking

Résumé

The X-ray structure of 2-(dibromomethyl)benzonitrile, featuring unexpectedly short C[triple bond, length as m-dash]N⋯Br halogen bond distances between a nitrile group and a C(sp3)-linked bromine atom, is presented. Despite the weak Lewis base nature of the nitrile N atom and absence of strong electron-withdrawing groups on the Br atom, π-stacking significantly enhances both the electron donor and acceptor capability of the interacting partners. As such, and beyond trivial (hetero)aromatic systems, the rationale of CN⋯Br halogen bonding can also be employed in purely aliphatic systems.

Domaines

Chimie
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Dates et versions

hal-04530325 , version 1 (03-04-2024)

Licence

Paternité - Pas d'utilisation commerciale

Identifiants

Citer

Kamil Kupietz, Rosa Maria Gomila, Thierry Roisnel, Antonio Frontera, Rafael Gramage-Doria. Shortening C≡N···Br-C sp3 halogen bonds via π-stacking. CrystEngComm, 2024, 26, pp.2131-2135. ⟨10.1039/D4CE00307A⟩. ⟨hal-04530325⟩
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